Holiday houses in Milwaukee
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Top-rated holiday rentals in Milwaukee
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Milwaukee holiday rentals
Other great holiday rentals in Milwaukee
Guest favourite
Guest suite in Sussex
4.99 out of 5 average rating, 125 reviewsGarden Retreat in law Suite
11–18 Sep
$271 NZD per night
Guest favourite
Loft in Milwaukee
4.83 out of 5 average rating, 399 reviewsCharming Loft - sparkling clean-walk everywhere
25 Mar – 1 Apr
$264 NZD per night
Guest favourite
Apartment in Milwaukee
4.91 out of 5 average rating, 186 reviewsCharming upper Brady St. 2+bedroom upper unit
3–10 Jan
$231 NZD per night
Superhost
Apartment in Milwaukee
4.85 out of 5 average rating, 171 reviewsCozy Basement Space In Bay View by Lake Michigan
4–11 Jan
$121 NZD per night
Guest favourite
Guesthouse in Milwaukee
4.86 out of 5 average rating, 273 reviewsCozy Brewer's Hill Coach House
8–15 Feb
$226 NZD per night
Guest favourite
Home in Milwaukee
5.0 out of 5 average rating, 36 reviewsBright 1 Bed in the heart of Bay View - w/ Parking
7–14 Jan
$219 NZD per night
Guest favourite
Apartment in Milwaukee
4.99 out of 5 average rating, 91 reviewsLakeview Downtown Milwaukee Condo
6–13 Dec
$312 NZD per night
Guest favourite
Home in Milwaukee
5.0 out of 5 average rating, 13 reviewsEntire Cozy Cottage! Pet Friendly, No Cleaning Fee
8–15 Dec
$264 NZD per night
Quick stats about holiday rentals in Milwaukee
Total rentals
2.4K properties
Rentals with dedicated workspaces
1.4K properties have a dedicated workspace
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
770 properties allow pets
Family-friendly rentals
1.5K properties are a good fit for families
Total number of reviews
94K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- Madison Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Monthly Rentals Milwaukee
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- Rentals with an EV charger Milwaukee
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- Rentals with a fire pit Milwaukee
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- Hotel rentals Milwaukee
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- Rentals with lake access Milwaukee
- Rentals with a washing machine and dryer Milwaukee
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